Dear John addresses a bad rebound, a friend who wants a pot-head to get a “real job”, and a cute landlord.

Here’s the story: I’m newly separated from my husband. I’ve had a difficult marriage in which I felt silenced and unheard and tried to cope for years by becoming a version of myself to my husband’s liking. Everything since the first few weeks of marriage made me feel like I should be running for the hills, which is something I didn’t articulate until recently. I have everything really going for me. I have a high-powered, good-paying job. I bought an apartment. I supported us. All of this is to give you context.

In any case, when I decided to divorce my husband, I met this guy who has been in a relationship with his girlfriend for ten years (except for a short break). He pursued me and I guess I was game because we got along so ridiculously well as friends that I can honestly say I’ve never had this kind of connection with anyone. Also it was just so totally unexpected—I mean it didn’t even enter my mind he was pursuing me until he kissed me. He convinced me to invest despite my skepticism. Anyway, we had a few weeks of craziness where he filled my head with irrational crap about how he wished we had met before I met my husband, how we should run away with each other, how once I left my husband for good I would move in with him, etc. To which I was obviously saying, “You’re crazy; we can talk about this in a year if ever.”

The problem is that he opened a part of me that has been closed for years, if it was ever opened in the first place. Eventually, he decided that he didn’t want to mess up his life (which I get) and decided to call it off between us. Still, he would make comments about how he didn’t want me to be just another girl (he believes everybody cheats and that every few years it would happen—which I think is bull, by the way) and okay, I get that it’s over, and really I am in no position to get into a relationship nor do I want to be in one. The problem is I see this guy all the time (he’s in my group of friends, though he never brings along his girlfriend) and when he’s drinking we end up just chilling together and having a great time together. No line ever gets crossed anymore, but the conversations are magical.

So basically, I just can’t get over him. Here I should be mourning my actual relationship, and I can’t do anything but think about him. How do I get over this guy? I don’t want to keep feeling so volatile, and even though I know all the logical arguments and repeat them to myself, there is this weird part of me deep within carrying this flame like I feel we’re going to be together sooner or later. I just want to get it out. I want to feel normal and fabulous the way I usually do and be prepared to maybe meet someone else and start my life over again—those parts that need starting over that is.

Thanks for any advice you can give me.

Sincerely,Dazed And Confused

Dear Dazed,

However you do it, you’ve got to give yourself time to be completely away from this guy for a couple of reasons. First, you’re right—your marriage is collapsing and you’re not giving yourself any time to think about that. I’m not saying you have to grieve about it—it sounds like something you can celebrate being away from, actually. But what did you learn from it? What did you learn about yourself and why you stayed in something so stultifying for so long? You’re not considering these things because you’ve fallen for this guy instead. Is it possible you’re using this infatuation to avoid some painful self-examination?

The second reason is simply that this guy sounds like such bad news. You can’t get over a guy who is accidentally considerate enough to actually warn you he will definitely cheat on you? So you have great conversations. How are you going to feel when the conversation is about how he spent last weekend with one of your friends? And he told you this was how it was going to be!

You need some time to be alone and contemplate the past few years. It’s way too soon for another relationship, especially with this manipulative, selfish man. If being without a partner leaves you feeling like there’s a hole in your life, the best thing you can do is think about why you feel that way. The worst thing you can do is fill it with him.

Dear John,

I first want to thank you for your extremely insightful and well-written responses. I read with a critical eye yet tend to agree with your points almost all the time.

That’s the reason I wanted to reach out to ask for your opinion: I grew up with my buddy—he has always been, and remains, a great and loyal friend. However, as I’ve graduated college and gotten a “real” job, he has remained unemployed (for about 2 years) and obsessed with marijuana. Although other friends and I have offered to get him various jobs, he just wants to “focus” on his weed. He smokes every day but is a legal caretaker, so he is not doing anything illegal. His big plan is to sell it to dispensaries (which are not even open yet), and a lot of other growers are trying to do the same. He still lives with his parents and has no money.

I don’t want to impose any standards or judgment on him, but there is no reason he needs to stay at home to watch his plants all day. He can easily get a job (at least part time). The fact that he doesn’t makes him seem very lazy, and he’s not advancing his career or life. You can’t support a family on growing weed in a basement. My main concern is for him, but on a more selfish note, our friends are getting very frustrated that he never has money to contribute when we all hang out. We’ve all pushed him to get a job, and he knows where we all stand. Do we push even harder, or try to separate our friendship from his career aspirations?

Thanks in advance for any advice!

Signed,A Friend With Weed

Dear Friend,

It sounds like you’ve all made it clear you think it’s time for this guy to stow the bong at least long enough to go to work every day. And he’s made it equally clear he’s not interested. At this point, you’ve crossed the border separating concerned advice from nagging. Your buddy is an adult and he’s decided what he wants to be doing with his life right now. Let him do it.

What he must understand, though, is choices have consequences. I would let him know you’re not going to bring up his “lifestyle” any more, but if he ever decides he’d like to emerge from the basement and earn a paycheck, you’ll be glad to help him find a job. Until that day comes, if you don’t mind paying for his beers, then do so. That seems a small price to pay if you enjoy his company. Don’t feel obliged to, though, because you’re not. And when the group gets together to do something fun that your jobs make possible, like going skiing for the weekend, let him know that he’s not being excluded, but you figured he didn’t have any money so there was no point in inviting him. He can’t have it both ways.

Dear John,

I am writing to you because I am a little confused with what to do about a girl I like.

I am currently living overseas and am going home shortly to decide whether I will come back long-term to work in the community where I am currently living and working. The chance of my coming back is quite high. The problem I am having is that I really like the girl who is my housemate, but she is also my landlord, and if I decide to come back the living arrangements will continue as they are for the time being. We get along great as friends and sometimes I get the feeling that she may be interested in me, too (although I have been wrong about reading a girl’s signals before), but I am thinking that asking her out on a date may be crossing a line due to the current situation. I don’t know if I should just straight up ask her on a date, talk to her about it first, or just leave it be for now.

Your thoughts on my situation would be greatly appreciated.

Sincerely,Friend (For Now)

Dear Friend,

This is the quintessential “nothing ventured, nothing gained” situation. And I think the timing works in your favor.

Let this woman know how you feel. Ask her out. If she says yes, great. If she says no, you can go back home and have some time away from her to get past the disappointment and think about whether it’s worth exploring other living arrangements when and if you return.

Life’s too short not to let her know you’re attracted to her. It could be a lot longer and it would still be too short to keep feelings like this to yourself.

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